1-Benzylpiperazine → HCID 24756555, compound

HRID 885874Notes

Reaction equation

HRID 885874 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCCC1[O:20][NH:21][C:22](/[CH:24]=[CH:25]/[C:26]1[CH:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[C:34]([C:36]2[CH:47]=[CH:46][C:39]([CH2:40]OS(C)(=O)=O)=[CH:38][CH:37]=2)=[O:35])=[CH:28][CH:27]=1)=[O:23]>CN(C=O)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:40][C:39]2[CH:38]=[CH:37][C:36]([C:34](=[O:35])/[CH:33]=[CH:32]/[C:29]3[CH:30]=[CH:31][C:26](/[CH:25]=[CH:24]/[C:22]([NH:21][OH:20])=[O:23])=[CH:27][CH:28]=3)=[CH:47][CH:46]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 759941-BenzylpiperazineHCID 59312563HCID 59312563, compound

Product 1

HCID 24756555HCID 24756555, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Benzyl-piperazine (40 mg, 0.22 mmol) was added to a stirred mixture of methanesulfonic acid 4-((E)-3-{4-[(E)-2-(tetrahydro-pyran-2-yloxycarbamoyl)-vinyl]-phenyl}-acryloyl)-benzyl ester (prepared as described in Preparation 5, 90 mg, 0.185 mmol) and TEA (0.052 ml, 0.37 mmol) in DMF (2 ml). The resulting solution was stirred at room temperature for 1 h. The mixture was diluted with water and extracted with hot AcOEt. The organic phase was washed with water, dried over Na2SO4 and evaporated in vacuo. The crude reaction mixture was triturated with di-isopropylether/DCM, filtered and the resulting powder was suspended in DCM and treated with HCl/Et2O for 1 h. The solid was filtered and washed with DCM to give 28.1 mg of (E)-3-(4-{(E)-3-[4-(4-benzyl-piperazin-1-ylmethyl)-phenyl]-3-oxo-propenyl}-phenyl)-N-hydroxy-acrylamide as its bis-hydrochloride salt.

Workup

  1. extractionextracted with hot AcOEt
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude reaction mixture
  6. customwas triturated with di-isopropylether/DCM
  7. filtrationfiltered
  8. additiontreated with HCl/Et2O for 1 h
  9. filtrationThe solid was filtered
  10. washwashed with DCM

Sources & evidence

ORD record
ord-8823ce4485714cfb9cfbd6dc27ea74d4
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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